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532657

Sigma-Aldrich

(4bS)-trans-8,8-Trimethyl-4b,5,6,7,8,8a,9,10-octahydro-1-isopropylphenanthren-2-ol

98%

Synonym(s):

Totarol

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About This Item

Empirical Formula (Hill Notation):
C20H30O
CAS Number:
511-15-9
Molecular Weight:
286.45
MDL number:
MFCD02094185
UNSPSC Code:
12352002
PubChem Substance ID:
24877903

Assay

98%

optical activity

[α]20/D +41°, c = 1 in chloroform

mp

128-132 °C (lit.)

SMILES string

CC(C)c1c(O)ccc2c1CC[C@H]3C(C)(C)CCC[C@]23C

InChI

1S/C20H30O/c1-13(2)18-14-7-10-17-19(3,4)11-6-12-20(17,5)15(14)8-9-16(18)21/h8-9,13,17,21H,6-7,10-12H2,1-5H3/t17-,20+/m0/s1

InChI key

ZRVDANDJSTYELM-FXAWDEMLSA-N

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
06302HI

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M Dufour et al.
International journal of food microbiology, 85(3), 249-258 (2003-07-25)
Despite numerous papers being published on the use of hurdle technology to control food-borne pathogens or spoilage organisms, there is no commonly accepted methodology to quantify the level of synergistic activity. This paper describes a method to quantify in vitro
C L Wu et al.
Journal of Asian natural products research, 3(3), 241-246 (2001-08-09)
Two minor diterpenoids, 15(16)-peroxy-3, 13-clerodadien-18-oic acid (4) and totarol (7), were isolated from the liverwort Schistochila acuminata. The former is a further oxidized cyclic peroxide from the major component. The latter is a rearranged abietane alcohol which skeleton was found
C R Mateo et al.
Biochimica et biophysica acta, 1509(1-2), 167-175 (2000-12-19)
(+)-Totarol, a diterpene extracted from Podocarpus totara, has been reported as a potent antioxidant and antibacterial agent. Although the molecular mechanism of action of this hydrophobic molecule remains unknown, recent work made in our laboratory strongly suggests that it could
G B Evans et al.
Bioorganic & medicinal chemistry, 8(7), 1653-1662 (2000-09-08)
Alterations of the C-12 and C-13 aromatic ring substituents of totarol (1) afforded the series of derivatives 2-14, and introduction of substituents at C-12 gave exclusively 2a-14a. The majority of these analogues were tested in vitro against the following organisms:
Michelle B Kim et al.
Organic letters, 12(15), 3324-3327 (2010-07-06)
An efficient, convergent synthesis of totarol by a diastereoselective epoxide/alkene/arene bicyclization is described. The reported synthesis enables the preparation of related diterpenes totaradiol and totarolone as well as previously unavailable derivatives that exhibit comparable inhibition of the bacterial cell division
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